Hydrochloric Acid → HCID 23513888, compound

HRID 353585Notes

Reaction equation

HRID 353585 reaction equation
C(O[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([C:14]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:13])C#CC.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.C(N([CH2:37][CH3:38])CC)C.Cl.[CH3:40][CH2:41][O:42]CC>CO.ClCCl>[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:17]2[CH2:16][CH2:15][C:14]([S:12]([C:7]3[CH:6]=[CH:11][C:10]([O:42][CH2:41][C:40]#[C:37][CH3:38])=[CH:9][CH:8]=3)=[O:13])([C:20]([OH:22])=[O:21])[CH2:19][CH2:18]2)=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 23513839HCID 23513839, compound

Product 1

HCID 23513888HCID 23513888, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(But-2-ynyloxy-benzenesulfinyl)-piperidine-4-carboxylic acid hydroxamide hydrochloride (prepared from example 81) (0.162 g, 0.434 mmol) and 4-bromobenzylbromide (0.120 g, 0.478 mmol) in methanol was added triethylamine (0.13 mL, 0.91 mmol). After 4 h the reaction mixture was concentrated in vacuo and chromatographed on silica gel (methanol/dichloromethane) to give an oily solid which was dissolved in dichloromethane. To the solution was added 1N hydrochloric acid in ether (1 mL). Concentration in vacuo gave 1-(4-Bromo-benzyl)-4-(4-But-2-ynyloxy-benzenesulfinyl)-piperidine-4-carboxylic acid hydroxamide hydrochloride as a tan solid (0.102 g). 1H NMR (dmso d6, 300 MHz) δ1.85 (t, 3H, CH3, J=2.2 Hz), 1.9-3.5 (m, 8H, CH2), 3.87 (S, 3H, OCH3), 4.3 (bd s, 2H, NCH2Ar), 4.82 (q, 2H, OCH2, J=2.2 Hz), 7.0-7.8 (m, 8H, ArH), 9.2-11.1 (m, 3H, NH, NHOH). Electrospray MS m/z 505.1/507.2 (M+H)+.

Workup

  1. concentrationAfter 4 h the reaction mixture was concentrated in vacuo
  2. customchromatographed on silica gel (methanol/dichloromethane)
  3. customto give an oily solid which
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-186fa47caeab4b338683f84dab482ad8
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

Loading…